Potassium Phosphate, Tribasic → HCID 86665695, compound

HRID 81072Notes

Reaction equation

HRID 81072 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([S:14][CH3:15])[C:3]=1[C:16]#[N:17].[CH:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1B(O)O)=[O:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([S:14][CH3:15])[C:3]=1[C:16]#[N:17])=[O:19]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 86665696HCID 86665696, compound

Product 1

HCID 86665695HCID 86665695, compoundYield 71.6%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-4-(methylthio)-2,3′-bipyridine-5-carbonitrile (57.7 mg, 0.220 mmol), 2-formyl-4-methoxyphenylboronic acid (83.4 mg, 0.463 mmol), aqueous potassium phosphate (550 μL, 1.100 mmol) and palladium tetrakis(triphenylphosphine) (16.1 mg, 0.014 mmol) in N,N-dimethylformamide (1 mL) was pumped under vacuum and backfilled with nitrogen twice. After 2 h at 90° C., the mixture was cooled to room temperature, diluted with methanol (2 mL) and filtered to give 6-(2-formyl-4-methoxyphenyl)-4-(methylthio)-2,3′-bipyridine-5-carbonitrile as brown solid (56.9 mg, 62% yield). 1H NMR (500 MHz, CDCl3) δ ppm 9.99 (1H, s), 9.20 (1H, δ, J=1.92 Hz), 8.72 (1H, dd, J=4.67, 1.65 Hz), 8.34 (1H, dt, J=7.97, 1.92 Hz), 7.71 (1H, δ, J=8.52 Hz), 7.57 (1H, δ, J=2.75 Hz), 7.56 (1H, s), 7.45-7.49 (1H, m), 7.44 (1H, dd, J=8.11, 4.81 Hz), 3.95 (3H, s), 2.74 (3H, s); MS (ES+) m/z: 362 (M+H); LC retention time: 3.088 min (analytical HPLC Method A).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-8355002b57be46e0a128b3914aba5a06
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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